Five Reasons Why Every Entrepreneur Should Learn to Sail: A Tribute to My Dad on Father’s Day

My father first introduced me to sailing when I was about 10 years old. It was no fancy upscale introduction. We frequently went out for a sail on a scruffy little mud-bottom lake in my hometown in the north suburbs of Chicago. My first memories are aboard a flimsy yet fun and functional boat called a “Butterfly” with a simple centerboard, sail, tiller, and not much room for more than two men (or Dad and his daughter) and a few cans of his favorite hydrator. The topside was a sky blue and on sunny days I fondly remember the colors all pleasantly blending together as the water glimmered. My Dad eventually upgraded to a 16’ Catamaran called the Tequila Sunrise. We spent just about every weather prevailing weekend when I was 16 making that boat howl. I’d fearlessly strap myself into a trapeze and hang over the high side pontoon as we whizzed across the lake. The feelings of freedom contradicted the fact that I was highly restrained. When that gem of a boat capsized you’d hopefully be thrown from the trapeze and have to work your hardest to pull on the pontoon to get it back up. Frankly it was easier than it sounds even with my flyweight high school frame.

When I lost my Dad six years ago I inherited the boat he sailed until his last days when dementia robbed him of his sailing skills along with the memories he had made for me. As I reflect today on Father’s Day, I dearly hold those memories in my heart. I am so thankful to my Dad for introducing me to sailing. It has cultivated important skills that have been of benefit to me throughout my life and career. 

Here are five to consider as you navigate your future:

Leadership: You can’t be a namby-pamby and be at the helm of a boat. Whether you are cruising or racing you are in charge and that must be clear to everyone on board for safety and success. As communications training experts, we know you must be decisive and direct so your crew knows where they should be and what they should be doing. Sometimes captains yell. While that isn’t really acceptable in the business environment, if a boom is coming straight toward a distracted inexperienced crew member’s head quick commands must be made without dilly dallying. You don’t need to yell the command using fowl language but you better yell fast and loud and be ok with it. This may be uncomfortable for some yet as you get more skilled it becomes first nature. Figuratively it is no different when managing employees at your company. Just leave out the expletives and don’t raise your voice.

Confidence: Like running a business, sailing has unpredictable aspects to it. Many things can go wrong on a boat. You are dealing with the elements of nature, the technical aspects of a boat and the varying personalities of a crew. There are lots of predictive tools available to help weather through any conditions. It is up to you to learn and employ them. And it is crucial that you carefully consider the skills and strengths of your crew.  There is nothing more confidence building than getting all of these variables right so that you have a great sail, win the regatta or win the business. Tap technology to bring efficiencies to your business.  Be prepared to make performance-based decisions to change around your crew so that you put forward the strongest team. Your job is to lead, make hard decisions and do it with confidence. Sometimes just learning how to get off the dock safely is a very powerful, confidence-building starting point.  

Endurance: Sailing is a sport. Like in business, you can get knocked around. As an entrepreneur you must have the endurance to weather through high winds and rough waves. Maybe one day you get smacked in the face by an unpredictable wave. Take it in stride. Pull yourself up and hit it again. Find your life preserver and holdfast because another one is going to come. Evaluate with your crew what you learned and what measures and tools can be employed to minimize the likelihood of it happening again. Building endurance takes planning and a strong strategy not just jumping in the boat and heading out to sea without checking conditions and calculating your route.

Collaboration: Sailing requires a crew that has mutual respect for one another and for you as the captain. There are so many variables to consider to optimize the pleasure and success of your sail and as the captain you have to adjust accordingly. You bring your A Team to face a difficult high risk day even if you disappoint a few people. You cultivate your B Team when there is a good deal to learn with varying yet lower risk. You advise all of your crew about areas of improvement and skills needs to advance and improve. And you always keep a weathered eye out for a Fletcher Christian who has the potential to negatively impact your performance, undermine you and unfavorably influence your crew.

Ballast: Building a business take immense energy. Even if you have a deep passion for your business, you need balance in your life so that you don't get stuck in the bilge. Sailing is a wonderful outlet from the churn and burn of a working life. Yes it can be unpredictable but it is immensively fun too. You have the beauty of our world around you which can help bring the ballast you need in life to face the challenges of a new day. Additionally, the sailing community is filled with colorful characters from all walks of life and is globally vibrant.

A salute today to Dads around the world who cultivate lifelong skills like sailing in their children's lives. And to my Dad Daniel Reilly, the salt of the Earth and now among the wind and stars.